Potassium Carbonate → HCID 86700259, compound

HRID 879450Notes

Reaction equation

HRID 879450 reaction equation
[CH3:1][C:2]1[C:3](=[O:24])[NH:4][C:5](=[O:23])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10](B3OC(C)(C)C(C)(C)O3)[CH:9]=2)[CH:7]=1.Br[C:26]1[S:27][C:28]2[C:34]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)=[C:33]([C@H:42]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[C:43]([O:45][CH2:46][CH3:47])=[O:44])[C:32]([CH3:53])=[CH:31][C:29]=2[N:30]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:49]([O:48][C@@H:42]([C:33]1[C:32]([CH3:53])=[CH:31][C:29]2[N:30]=[C:26]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([N:6]4[CH:7]=[C:2]([CH3:1])[C:3](=[O:24])[NH:4][C:5]4=[O:23])[CH:9]=3)[S:27][C:28]=2[C:34]=1[C:35]1[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=1)[C:43]([O:45][CH2:46][CH3:47])=[O:44])([CH3:50])([CH3:51])[CH3:52]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetateHCID 86700260HCID 86700260, compound

Product 1

HCID 86700259HCID 86700259, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture 5-methyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine-2,4(1H,3H)-dione (50 mg, 0.154 mmol), (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (51 mg, 0.103 mmol), Pd(PPh3)4 (12 mg, 0.01034 mmol) and 2M potassium carbonate (0.15 mL, 0.309 mmol) was heated at 105-120° C. for 5 h. Reaction mixture was stirred over the weekend at rt, diluted with ethyl acetate and washed with brine, dried (MgSO4), filtered, concentrated and purified by Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA). Product-containing fractions were diluted with ethyl acetate, washed with saturated sodium bicarbonate solution/brine. Organic layer was dried (MgSO4), filtered, and concentrated to give desired product. LCMS-ESI+: calc'd for C33H33ClN3O5S: 618.2 (M+H+); Found: 618.2 (M+H+).

Workup

  1. customReaction mixture
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA)
  7. additionProduct-containing fractions were diluted with ethyl acetate
  8. washwashed with saturated sodium bicarbonate solution/brine
  9. dry with materialOrganic layer was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-5fbaccd9ec4a47d49850bcbd3bd7f3aa
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…